7-Bromo-3-methylnaphthalen-1-ol → 1-Naphthol, 3-methyl-

HRID 514110

Reaktionsgleichung

Reaktionsgleichung von HRID 514110
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:13])[CH:8]=[C:9]2[OH:12])=[CH:4][CH:3]=1>[Pd].CCO>[CH3:13][C:7]1[CH:8]=[C:9]([OH:12])[C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[CH:2][CH:11]=2

Komponenten

4

Edukt 1

HCID 671262827-Bromo-3-methylnaphthalen-1-ol

Produkt 1

HCID 261351-Naphthol, 3-methyl-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

A slurry of 7-bromo-3-methylnaphthalen-1-ol (100 mg, 0.421 mmol), 10% w/w Pd/C (45 mg, 42.1 μmol Pd), and absolute EtOH (2.0 mL) was purged under vacuum and backfilled with H2 from a balloon several times. The suspension was stirred under a balloon of H2 at 23° C. overnight. The reaction was filtered over Celite, the cake was washed with EtOAc. The filtrate was concentrated and dissolved in DCM. The solution was wet-loaded onto a 12 g “gold” ISCO silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product (yield was not found). 1H NMR (400 MHz, CDCl3) δ 8.10 (d, J=7.8 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 7.47-7.39 (m, 2H), 7.22 (s, 1H), 6.67 (s, 1H), 2.45 (s, 3H).

Aufarbeitung

  1. filtrationThe reaction was filtered over Celite
  2. washthe cake was washed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. dissolutiondissolved in DCM
  5. custompurified by flash chromatography (ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-76f4a0cb7efe4d6ebbadd81f5cd2e57d
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102614B2

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